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Reacción de deshidratación de alquenos y alquinas sustituidos por hidroxilo en el complejo Ru(2) S(2)
Kazuko Matsumoto1, Yoshihiro Moriya, Hiroyasu Sugiyama
1Department of Chemistry, School of Science and Engineering, and Advanced Research Institute of Science and Engineering, Waseda University and Japan Science and Technology Corporation, 3-4-1 Ohkubo, Shinjuku, Tokyo 169-8555, Japan. kmatsu@waseda.jp
Journal of the American Chemical Society
|October 31, 2002
Resumen
Los complejos de rutenio reaccionan con alquenos y alquinas sustituidos por hidroxilo, sometidos a deshidratación para formar nuevas estructuras de anillo C-S. Este estudio explora las reacciones inter e intramoleculares, que producen diversos complejos organometálicos.
Área de la Ciencia:
- Química organometálica Química orgánica de los metales.
- Coordinación Química de la Coordinación
- Química sintética de la química sintética.
Sus antecedentes:
- Los complejos de rutenio son catalizadores versátiles en la síntesis orgánica.
- Las reacciones de deshidratación son fundamentales para la formación de nuevos enlaces químicos y estructuras cíclicas.
- Comprender la reactividad de los complejos de rutenio que contienen azufre es crucial para el desarrollo de nuevas metodologías sintéticas.
Objetivo del estudio:
- Para investigar las reacciones de un complejo específico de rutenio, [[Ru(P(OCH(3)) ((3)) ((2) (((CH(3)) ((3))) ((3))) ((2))) (((mu-S(2))))) ((CF((3) (((SO(3)) ((4) (1), con varios alquenos y alquinas sustituidos por hidroxilo.
- Para dilucidar los mecanismos de deshidratación inter e intramolecular en estas reacciones.
- Para sintetizar y caracterizar nuevos complejos cíclicos que contienen rutenio.
Principales métodos:
- Reacción del complejo 1 con el alcohol aliloico, el 3-buten-1-ol, el 2-propin-1-ol, el 2-butin-1-ol y varios diolos.
- Aislamiento y caracterización de productos intermedios y finales mediante técnicas espectroscópicas.
- Análisis de las vías de reacción, incluyendo la activación de enlaces C-H y la deshidratación.
Principales resultados:
- Formación de un complejo de anillo de cinco miembros C(3) S(2) (2) mediante deshidratación intermolecular y activación de C-H con alcohol aliloico.
- Síntesis de un complejo de anillo de seis miembros C(4) S(2) (3) a través de la deshidratación intramolecular con 3-buten-1-ol.
- Generación de productos de homoacoplamiento y acoplamiento cruzado (4-7) a partir de reacciones con alcoholes propargílicos, que incluyen deshidratación intermolecular.
- Formación de complejos furilo (8-9) y otras estructuras únicas (10-11) a partir de reacciones con diolos y alquinas metoxisubstituidas, que muestran diversas vías de deshidratación y de escisión de enlaces S-S.
Conclusiones:
- El complejo de rutenio 1 media efectivamente en las reacciones de deshidratación inter e intramoleculares con alcoholes insaturados.
- El estudio demuestra la formación de diversas estructuras organometálicas cíclicas, destacando la utilidad de este complejo de rutenio en la química sintética.
- Las reacciones observadas proporcionan información sobre la formación de enlaces C-S, la activación de C-H y nuevas estrategias de ciclización que involucran al rutenio.
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